Director, People Operations & Systems

Whatnot is the largest livestream shopping platform in North America and Europe to buy, sell, and discover the things you love. Whether it's trading cards, fashion, electronics, or live plants, our sellers are building real businesses across hundreds of categories. We're building live commerce at a scale that's never been done in the West, and there's no playbook to copy. The people here are shaping how an entirely new industry develops.

As a remote co-located team, we're inspired by our values and anchored in hubs across the US, UK, Ireland, Poland, Germany, and Australia. We move fast, stay close to our users, and focus on the work that drives the most impact.

We're one of the fastest growing marketplaces and were recently named the #1 Best Startup Employer in America by Forbes. Check out the latest Whatnot updates on our news and engineering blogs and join us as we enable anyone to turn their passion into a business and bring people together through commerce.

We are seeking a Director, People Operations & Systems to build and lead Whatnot's global people operations infrastructure as we scale from 1,000 to 1,500+ employees in 2026 and expand into new international markets. This role owns the full People Operations function — onboarding and offboarding, employee lifecycle administration, HRIS and people systems strategy, compliance and documentation, and the shared services model that enables the entire People organization to operate with excellence at scale.

You'll need to be both a systems architect (designing scalable processes, selecting and implementing technology, building analytics capabilities) and an operational executor (ensuring flawless delivery of core people services, managing compliance risk, solving urgent employee issues).

• You'll report directly to our Chief People Officer, and work in tight partnership with our Head of Total Rewards, People Business Partners, Finance, Legal, and IT to build the operational backbone of our People function — ensuring every employee has a seamless experience from offer through exit, that people data drives business decisions, and that our systems enable growth.

• Own end-to-end employee lifecycle operations globally, including onboarding, changes (transfers, promotions, leaves), offboarding, documentation management, background checks, I-9/work authorization, and compliance administration.

• Build and scale the People Help Desk as the front door for all employee questions and requests — ensuring fast response times, proactive issue resolution, knowledge base development, and continuous improvement of self-service capabilities.

• Lead People systems strategy and implementation, including Workday, Complete, equity platforms, and integration across Finance, IT, and productivity tools.

• Partner with People Business Partners and Total Rewards to deliver People analytics and insights — quarterly business reviews, attrition analysis, organizational design modeling, headcount planning, and ad hoc strategic analysis.

• Design and implement scalable people operations processes — documentation, workflows, approval chains, compliance checkpoints — that maintain quality and employee experience while enabling rapid growth and international expansion.

• Manage global compliance and reporting in partnership with Legal.

• Build and lead the shared services model for the People team defining scope, staffing, SLAs, and ways of working that allow People Business Partners and Centers of Excellence to focus on strategic work rather than transactional execution.

• Drive people systems optimization across vendor management, change management for system implementations, integration planning, security and access management, and continuous enhancement of system capabilities.

• Build, hire, and develop a high-performing People Operations team setting vision, developing talent, and fostering operational excellence.

• Lead special projects including international expansion (new country setup, entity formation, systems configuration), and transformation initiatives (shared services launch, new HRIS implementations).

We offer flexibility to work from home or from one of our global office hubs, and we value in-person time for planning, problem-solving, and connection. Team members in this role must live within commuting distance of our San Francisco, New York City, Seattle, or Los Angeles hubs.

People who do well at Whatnot tend to be comfortable figuring things out as they go, biased toward action, and genuinely curious about what they're building. They care more about outcomes than credit and stay close to the product and the people using it.

As the leader of Whatnot's People Operations & Analytics function, you should have 12+ years of progressive People Operations, HRIS, or People Analytics experience at high-growth tech companies, including significant time building operations infrastructure through hypergrowth and ideally pre-IPO phases, plus:

• Expert-level Workday experience across HCM, Compensation, Payroll, and Time Tracking. You've implemented, configured, and scaled Workday across multiple modules and know how to make it sing.

• Strong analytics chops including SQL, dashboards (Looker/Tableau), and statistical analysis. You turn messy data into insights that change how leaders make decisions.

• Track record scaling operations from scrappy to mature. You've built the processes, systems, documentation, and teams that take companies from "figuring it out" to "running like clockwork."

• International operations experience dealing with employment law across countries, coordinating global payroll, managing work authorization, and navigating multi-country compliance.

• Balance strategic vision with hands-on execution. You're equally comfortable presenting a 3-year roadmap to the CPO and jumping into Workday to debug a security role issue.

• Exceptional at stakeholder management and influence. You partner effectively with People leadership, Finance, Legal, and drive alignment on priorities across distributed teams.

• Experience building and leading teams, hiring and developing operations professionals, analysts, and systems specialists.

• Strong judgment on risk, compliance, and tradeoffs. You know when to move fast and when to slow down, when to automate and when the human touch matters.

• Generous Holiday and Time off Policy

• Health Insurance options including Medical, Dental, Vision

• Work From Home Support

  • Home office setup allowance

  • Monthly allowance for cell phone and internet

• Care benefits

  • Monthly allowance for wellness

  • Annual allowance towards Childcare

  • Lifetime benefit for family planning, such as adoption or fertility expenses

• Retirement; 401k offering for Traditional and Roth accounts in the US (employer match up to 4% of base salary) and Pension plans internationally

• Monthly allowance to dogfood the app

  • All Whatnauts are expected to develop a deep understanding of our product. We're passionate about building the best user experience, and all employees are expected to use Whatnot as both a buyer and a seller as part of their job (our dogfooding budget makes this fun and easy!).

• Parental Leave

  • 16 weeks of paid parental leave + one month gradual return to work *company leave allowances run concurrently with country leave requirements which take precedence.

Whatnot is proud to be an Equal Opportunity Employer. We value diversity, and we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, parental status, disability status, or any other status protected by local law. We believe that our work is better and our company culture is improved when we encourage, support, and respect the different skills and experiences represented within our workforce.